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OWA stopped working w/ SSL

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  • OWA stopped working w/ SSL


    I've followed this forum for years solving misc issues. I've now run into a problem that I can't find any input on. Thanks in advance for your help!

    My problem is that we have a 2008 Server SP2 w/ Exchange 2007 that's been running great. Fifty plus users, iPhones & Droids all sync no problem. OWA has been flawless until yesterday. We did intall about 40 updates over the last week and rebooted the night before last. OWA and phones stopped working after the reboot. Here's the details:

    1) Digicert SAN SSL cert - Digicert reissued yesterday and we reinstalled successfully. It wasn't expired, but we thought maybe something was corrupt. Digicert intermediary cert tests ok

    2) If we disable SSL, OWA works fine.

    3) Same problem internally and externally & no specific error in the logs that point us in a good direction

    4) We can telnet to the server externally on port 443 and we get a normal response from Exchange

    5) We have verified that bindings for SSL are assigned to the default web

    6) We have rebuilt the Default Website just in case

    7) There aren't any other patches available from Win Updates

    I've had another engineer with a deep background in Exchange take a look and he is also stumped

    I'm about to call Microsoft because it's been a long night...

    Thx., Jay

  • #2
    Re: OWA stopped working w/ SSL

    The easiest thing to do is remove the SSL certificate completely, then create a self signed certificate using new-exchangecertificate.
    That will confirm if SSL is working correctly.

    I still suspect that there is a problem with the certificate, or something is getting in the way. A self signed certificate will confirm if the problem is with that certificate or SSL in general.

    If the SSL stream is being interrupted then the browser can't establish the secure session and that will mean it doesn't work.

    Oh and to be picky, you can't turn SSL on an off. The most you can do is enable/disable require SSL, but that doesn't stop SSL from working, it just means it isn't enforced. The only way to disable SSL is to remove the binding from the web site.

    Simon Butler
    Exchange MVP

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    • #3
      Re: OWA stopped working w/ SSL


      Thanks for your response and I apologize, we did create a self-signed cert and that also failed. Knowing that, should we look at removing and reinstalling IIS?

      That's the only other idea I have.

      Thx., Jay

      PS. And picky is ok. We did "turn off" SSL


      • #4
        Re: OWA stopped working w/ SSL

        Few questions:

        1. OWA is not working with SSL on, whats the error message on IE when you access OWA?
        2. With SSL ON, does it work on the server?
        3. When you access OWA while SSL on, can you post the IIS logs which are logged at that time?
        4. Anything logged in events?

        Also in IIS-->DWS-->SSL settings-->Under 'Client Certifcates' make sure "IGNORE" is selected.

        Technical Director
        Ex-Microsoft (Exchange Client & Server Infrastructure Team), MCSA, MCSE, MCITP, MCTS & ITIL Foundation certified